Start by watching the video on 3 ways serendipity can lead to your dream job.

No two careers are alike. While some rely on careful planning and a solid plan to get where they’re going, others have gotten lucky and landed the job of their dreams through serendipity.

You can actually count me among the latter group. Throughout my life, I’ve transitioned through four successful careers, each of them coming to me through serendipity, not planning. But as a career professional, I know for a fact that you can’t trust that kind of luck for long. Fate and serendipity are unreliable. If you want to find a career you love, you need to do some tough legwork!

Whether you are currently employed or you are looking for a job, there is nothing more important than effective career management. The way that I do it is by asking myself a series of questions every few months to check in with how everything in my career is going. There is always something in your career that you could improve on!

What do you think would happen in your career if you asked yourself these questions every six months?

Your Plans

  • Do you have clearly defined current career goals?
  • Have you written them down?
  • What actions are you taking to reach those goals?

Job Title

  • What is your current job title?
  • Does it accurately reflect your current duties?
  • If not, what can you do to change it so it’s aligned with your day-to-day work?


  • Do you have an up-to-date resume?
  • When did you last update it?
  • Did you write it with a focus on the work you currently do?
  • Did you write it with a focus on the type of work you want to do in the future?


  • What are the details of your entire benefits package, such as healthcare coverage and maternity-leave policies?
  • Could you negotiate further benefits?

What Are You Learning?

  • What new skills or knowledge could help you in your job search?
  • How can you learn them?
  • Can you get on-the-job or more formal training?


  • What are your primary achievements?
  • Are these highlighted in your resume?
  • Are they measurable and documented?


  • Who are your professional peers?
  • Where can you meet them?
  • Who should you be talking to, both within and outside your company?

Career Mentor

  • Do you currently have a mentor?
  • Did you ever have a mentor?
  • If not, how can you get one?
  • Can you mentor someone else?

These are the types of questions a career coach should be able to help you answer. Never ignore serendipity, but don’t rely on it when it comes to your career. Instead, you need to be looking for guidance in assessing your career. You need to define and follow an action plan, then proactively manage it! Then, when serendipity comes along, you will be prepared to take advantage of it!

Guidance is one of the things that I offer my clients. I’ve been on both sides of the interview table and have helped hundreds of people find jobs. By answers this list of questions together, we can jumpstart your job search and make sure that you don’t have to rely on serendipity to land the career of your dreams!